Syntheses of novel 3-amino-2(1H)-thioxo-4(3H)-quinazolinones and evaluation of their immunotropic activity. Part III.
The synthesis of two series of derivatives containing the quinazolinone-4 moiety is described. 3-Amino-2(1H)-thioxo-4(3H)-quinazolinone (1) was subjected to reactions with halogenoketones and halogenoaldehydes, leading to the production of the corresponding ketones, aldehydes, Schiff bases, and 6-oxo-1,4,5-thiadiazin[2,3-b]quinazoline derivatives. Subsequently, 1 was condensed with selected alpha, beta-unsaturated carbonyl compounds, aldehydes, ketones, acid chlorides, and esters. The compounds were tested for their potential activity in a model of humoral and cellular immune response. The tests showed that the compounds exhibited differential immunotropic activities. Of particular interest is compound 19, exhibiting a strong stimulatory activity with regard to cellular immune response and compound 16 exerting a strong inhibitory action in both types of the immune response.
Nawrocka
W
W
Department of Technology of Drugs, Wrocław University of Medicine, Poland.
Zimecki
M
M
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D008808:Mice, Inbred CBA; D011799:Quinazolines / Q000138:chemical synthesis* / Q000494:pharmacology; D012756:Sheep; D013329:Structure-Activity Relationship
D000276:Adjuvants, Immunologic; D007166:Immunosuppressive Agents; D011799:Quinazolines